Sodium hydride → HCID 14651261, compound

HRID 232672Notes

Reaction equation

[Cl:1][C:2]1[C:3](F)=[C:4]([C:18]([CH3:23])=[C:19]([F:22])[C:20]=1[F:21])[C:5]([C:7](=[CH:13][NH:14][CH:15]1[CH2:17][CH2:16]1)[C:8]([O:10][CH2:11][CH3:12])=[O:9])=[O:6].[H-].[Na+]>>[CH:15]1([N:14]2[C:3]3[C:4](=[C:18]([CH3:23])[C:19]([F:22])=[C:20]([F:21])[C:2]=3[Cl:1])[C:5](=[O:6])[C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:13]2)[CH2:17][CH2:16]1

Participants

Reactant 2

HCID 24758Sodium hydride

HCID 178471857HCID 178471857, compound

Product 1

HCID 14651261HCID 14651261, compoundYield 18.1%

Procedure

Employing ethyl 2-(3-chloro-2,4,5-trifluoro-6-methylbenzoyl)-3-cyclopropylaminoacrylate (410 mg) and 60% sodium hydride (35 mg), the procedure of Reference Example is repeated to give ethyl 1-cyclopropyl-6,7-difluoro-8-chloro-5-methyl-1,4-dihydro-4-oxoquinoline-3-carboxylate (70 mg), as pale yellow powder (recrystallized from dichloromethane-n-haxane), m.p. 153-154° C.

Sources & evidence

ORD record: ord-1a661669825943b6ba89d4826406e731
Source dataset: uspto-grants-1997_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05591744

Reaction notes

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